2-Bromothiazole → HCID 67269896, compound

HRID 1039726

Reaction equation

HRID 1039726 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Si:7]([O:14][C@H:15]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])/[CH:16]=[N:17]/[S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CCOCC>[Si:7]([O:14][C@H:15]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[C@@H:16]([NH:17][S@:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 67269896HCID 67269896, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-bromothiazole (7.9 ml, 89 mmol) in 200 mL ether was cooled to −78° C. and treated with a solution of n-butylithium (36 ml, 89 mmol) (2.5N in hexanes). After stirring for 30 minutes the reaction mixture was slowly added to a cooled (−78° C.) suspension of (S,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (25.000 g, 59 mmol) in 100 mL ether. The reaction mixture was allowed to stir at −78° C. for one hour. The reaction mixture was quenched with MeOH and saturated NH4Cl solution. The organic solution was washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave (S)-N-((1R,2S)-2,3-bis(tert-butyldimethylsilyloxy)-1-(thiazol-2-yl)propyl)-2-methylpropane-2-sulfinamide (24.81 g, 83% yield).

Workup

  1. additionwas slowly added to
  2. temperaturea cooled
  3. stirringto stir at −78° C. for one hour
  4. customThe reaction mixture was quenched with MeOH and saturated NH4Cl solution
  5. washThe organic solution was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by column chromatography

Sources & evidence

ORD record
ord-788abf77555a4ba5957ce475d61de960
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Linked notes

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